Glycoside Synthesis from Anomeric Halides

Abstract

This chapter contains sections titled: Glycosyl Fluorides Background Synthesis of Glycosyl Fluoride Donors Fluorinating Reagents Glycosyl Fluorides from Hemiacetals Glycosyl Fluorides from Glycosyl Esters Glycosyl from Glycosyl Halides Glycosyl Fluorides from S-Glycosides Glycosyl Fluorides from Other Anomeric Moieties Glycosylation Using Glycosyl Fluorides as Glycosyl Donors A Weak Lewis Acid Cleaves the CF Bond. How Was the Glycosyl Fluoride Method Discovered? Various Promoters Employed in Glycosylation by the Glycosyl Fluoride Method Glycosylations Promoted by Various Promoters Glycosylation of Silylated Compounds as Glycosyl Acceptors Two-Stage Activation Procedure Protecting-Group-Based Strategy Application to Natural Product Synthesis Special Topics C-Glycoside Synthesis via O-Glycosylation Glycosyl Fluorides for the Synthesis of a Combinatorial Library Glycosyl Fluorides as Glycosyl Donors for Chemoenzymatic Synthesis Conclusions and Future Directions Typical Experimental Procedures Preparation of the Glycosyl Donors Glycosylation Using Glycosyl Fluorides as Glycosyl Donors References Glycosyl Chlorides, Bromides and Iodides Background Glycosyl Chlorides Preparation of Glycosyl Chlorides Reactions of Glycosyl Chlorides Glycosyl Bromides Preparation of Glycosyl Bromides Reactivity Patterns and Some Useful Reactions of Glycosyl Bromides Stereoselective Glycosylations Employing Glycosyl Bromides and Applications Glycosyl Iodides Preparation of Glycosyl Iodides Reactions of Glycosyl Iodides Conclusions General Procedure for One-Pot Glycosylation Using Glycosyl Iodides References